Methyl vinyl sulfone → 4-chloro-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline

HRID 547320Notes

Reaction equation

HRID 547320 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:13]2[N:14]=[CH:15][N:16]([CH2:17][C:18]([CH3:21])([OH:20])[CH3:19])[C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1.[CH:22]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH2:23]>O1CCCC1>[Cl:3][C:4]1[C:13]2[N:14]=[CH:15][N:16]([CH2:17][C:18]([CH3:21])([O:20][CH2:23][CH2:22][S:24]([CH3:27])(=[O:26])=[O:25])[CH3:19])[C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1

Participants

5

Reactant 3

HCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 98384584-chloro-alpha,alpha-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

Product 1

HCID 866134654-chloro-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 58 mg, 1.45 mmol) was added to a stirred solution of 1-(4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (described in U.S. Pat. No. 4,689,338 Example 189, Part D, 4.00 g, 14.5 mmol) in tetrahydrofuran (58 mL). After 5 minutes, methyl vinyl sulfone (3.10 g, 29.0 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 17 hours. The volatiles were removed under reduced pressure and the resulting oil was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane) to yield 4.3 g of 4-chloro-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline as a foam.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe resulting oil was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-22ff6cc8f5214c0586b5d4477e90b99b
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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